TWI462975B - Process for the production of pigment composition, colored composition for color filter obtained by said process, and color filter - Google Patents

Description

Method for preparing pigment composition, coloring composition for color filter obtained by the method, and color filter

The present invention relates to a process for producing a pigment composition having very excellent dispersibility in a vehicle, wherein the particles for color development have a fine particle size and a uniform particle diameter, and relate to a filter for using the above pigment composition. The colored composition of the color former and the color filter using the above colored composition. In particular, the present invention relates to a process for the preparation of a pigment composition which provides good color when it is used to disperse colored powder particles in an ink such as a gravure ink or an offset ink or a paint vehicle. A coating of gloss and high tint strength. The present invention also relates to a coloring composition for a color filter for preparing a color filter for use in a color liquid crystal display and a color image pickup tube element, and to a color filter formed using the above colored composition .

Some organic pigments, such as azo pigments, are synthesized to obtain fine and uniform particles by selecting appropriate reaction conditions. For other organic pigments such as polyhalogenated copper indigo pigments, the extremely fine and agglomerated particles produced in the synthesis can be increased and homogenized during post-treatment. For other organic pigments such as copper indigo pigments, a treatment called coloring is carried out, and the sizes of the coarse particles and the uneven particles produced in the synthesis are finely divided and homogenized at the time of post-treatment.

For example, copper phthalocyanine pigments have a beautiful color and high color strength and have various properties such as weather resistance and heat resistance, and thus they are widely used in a large amount in the coloring material industrial field.

In general, the copper phthalocyanine pigment is a reaction between phthalic anhydride or its derivative, urea and copper source, or benzene under normal pressure or pressure and in the presence or absence of a catalyst such as ammonium molybdate or titanium tetrachloride. Preparation of a reaction between phthalodinitrile or a derivative thereof and an organic solvent such as a copper source in an alkylbenzene, trichlorobenzene or nitrobenzene.

However, the synthesized indigo molecules are grown via continuous particles in their synthesis solvent, so that only coarse particles and acicular particles having a major axis diameter of about 10 to 200 μm are obtained. Therefore, as a coloring pigment for inks, paints, plastics, and the like, its value is very low, and this indigo is called blister copper indigo. Therefore, it is necessary to finely pulverize the crude copper indigo to obtain particles having high effectiveness in coloring, that is, particles having a particle diameter of about 0.01 to 0.5 μm.

As an industrial method for finely crushing crude copper indigo, various methods are known. For example, a so-called solvent salt grinding method is known (see JP-A-7-53889 and JP-A-5-43704) in which a small amount of a solvent such as diethylene glycol is added to copper indigo and sodium chloride. In the mixture, and by vigorous kneading with a ball mill, an attritor or a batch kneader, the thus wetted mixture is wet-milled. In this method, sodium chloride and diethylene glycol are removed from the kneaded mixture by washing with water, and then dried to obtain a copper indigo pigment having fine primary particles.

However, conventional batch kneaders have problems such as limited production scale, mass variations between batches due to their batch form, contamination with impurities due to their open structure, and contamination due to dust generation. surroundings. In addition, a large amount of energy is required for the finely divided organic pigments, and there are also limitations at the level of fine crushing. Further, when the obtained copper indigo pigment is dispersed in a printing ink such as a gravure ink or an offset ink or a vehicle of a coating material and the obtained copper indigo pigment is used, it is always necessary to improve the gloss of the coating product thereof. And color strength.

In the liquid crystal display, the liquid crystal layer sandwiched between the two polarizing plates controls the polarization angle of the first polarizing plate and controls the amount of light transmitted through the second polarizing plate, thereby performing display. The main liquid crystal display device is a display using a twisted nematic (TN) type liquid crystal. The liquid crystal display is capable of color display by providing a color filter between the two polarizing plates. In recent years, liquid crystal display devices have been used in televisions and monitors for personal computers. For this reason, color filters having high brightness and high contrast are increasingly required.

The color filter is composed of at least two thin strips of color filters of different colors arranged in parallel or crosswise on a surface of a transparent substrate such as a glass substrate, or fine filter sheets arranged horizontally and vertically in a constant order. The color filter sheets are fine, i.e., from a few micrometers to hundreds of micrometers, and the color filter sheets are systematically arranged in a predetermined array for each color.

Generally, in a color liquid crystal display device, a transparent electrode for driving liquid crystal by vacuum evaporation and sputtering is formed on a color filter, and an alignment film for aligning liquid crystal in a predetermined direction is formed thereon. In order to sufficiently exhibit the properties of the transparent electrode and the oriented film, it is usually required to be 200 ° C or higher, preferably 230. A transparent electrode and an oriented film are formed at a high temperature of C or higher. Therefore, recently, a method called a pigment dispersion method as a color filter is mainly employed, which uses a pigment having excellent light resistance and heat resistance as a colorant.

However, in general, a color filter in which a pigment is dispersed generally has a problem of light scattering because the pigment disturbs the polarization angle controlled by the liquid crystal. That is to say, light leaks when light should be intercepted (OFF state), and transmitted light when light should be transmitted (ON state). The problem at this time is that the luminance ratio (contrast) of the display between the ON state and the OFF state is low.

In order to realize a color filter having high contrast, the pigment contained in the color filter sheet is subjected to finely divided processing. As a method of finely pulverizing pigments, the solvent salt polishing method described above has been widely used in recent years.

The solvent salt grinding method is carried out by using a mechanical device such as sodium chloride or sodium sulfate and a water-soluble organic solvent having a high viscosity such as ethylene glycol, diethylene glycol or polyethylene glycol. A method of grinding particles to finely chop coarse pigment particles. Solvent salt milling is effective for finely divided and homogenized pigment particles. However, in order to achieve an improvement in the contrast of the color filter, it is required to use a pigment having finer and more uniform particles than the pigment particles obtained by the conventional salt milling method.

It is an object of the present invention to provide a process for preparing a pigment composition which overcomes the problems associated with conventional batch kneaders, such as production scale limitations, mass variations between batches, impurities due to its open structure, And polluting the working environment due to dust generation.

Another object of the present invention is to provide a method for preparing a pigment composition having finer particles with a smaller amount of energy than a conventional batch kneader, when the pigment is dispersed in a printing ink such as a gravure ink or an offset ink or When used in a vehicle for coatings, the pigment enables the coating to have high gloss and improved color strength, and even in applications requiring finer pigment particles, such as inks for inkjet printing or color filters. It is also possible to impart excellent properties.

Another particular object of the present invention is to provide a process for efficiently preparing fine pigments in a short period of time which cannot be obtained by conventional batch kneaders.

Another object of the present invention is to provide a coloring composition for a color filter comprising a pigment having fine and uniform particles and capable of forming a color filter having high contrast.

Another object of the present invention is to provide a color filter having high contrast by using the above colored composition.

According to the invention 1, there is provided a method for producing a pigment composition, which comprises kneading a mixture comprising an organic pigment, a water-soluble inorganic salt, a water-soluble organic liquid and a resin by a continuous kneader comprising a drive shaft and a ring A fixed disk, a rotating disk concentric with the fixed disk and rotating around the axis of the drive shaft, and a pulverizing space formed in a gap between the fixed disk and the rotating disk.

According to the invention 2, there is provided a process for producing a pigment composition, which comprises kneading an organic dye derivative, an anthracene derivative or the like by a continuous kneader a mixture of a derivative, an organic pigment, a water-soluble inorganic salt and a water-soluble organic liquid, each of the above derivatives having at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group The continuous kneading machine includes a drive shaft, an annular fixed disk, a rotary disk that is concentric with the fixed disk and rotates around the axis of the drive shaft, and a pulverizing space formed in a gap between the fixed disk and the rotary disk.

According to the invention 3, there is provided a coloring composition for a color filter comprising a pigment carrier and a pigment composed of a transparent resin, a precursor thereof or a mixture thereof, wherein the pigment comprises inclusion by kneading with a continuous kneader a fine organic pigment obtained by mixing a mixture of an organic pigment, a water-soluble inorganic salt and a water-soluble organic liquid, the continuous kneader comprising a drive shaft, an annular fixed disk, a rotating disk concentric with the fixed disk and rotating around the axis of the drive shaft, and A smashing space formed in a gap between the fixed disk and the rotating disk.

The present invention also provides a color filter comprising a color filter sheet formed of the above colored composition.

According to the method for producing a pigment composition provided by the present invention, the production scale is less restricted than the conventional batch kneader, and therefore an appropriate amount of timely production is possible. Furthermore, the method of the invention has the following advantages. The quality change between product batches is small. Since the kneader used is a closed kneader, it is possible to overcome the problem of contaminating the working environment and mixing impurities due to the generation of dust. The particles can be pulverized into fine particles with a small amount of energy. When the organic pigment obtained by the process of the present invention is dispersed in an ink such as a gravure ink or an offset ink or paint, the pigment imparts good gloss and improved color strength to the coated article. In addition, it is especially suitable for applications that require transparency.

According to the coloring composition for a color filter provided by the present invention, since the colored composition contains an organic pigment having fine particles having a uniform particle diameter which is generally difficult to obtain, the coloring composition of the present invention can form a contrast more than ever. High color filter.

First, a continuous kneading machine used in the present invention will be described with reference to Fig. 1 . Fig. 1 is a cross-sectional side view showing a specific example of a continuous kneading machine used in the present invention. As a preferred example of the continuous kneader used in the present invention, a continuous kneader disclosed in JP-B-2-92 can be used. For example, a continuous kneader 10 ("Miracle K.C.K.") supplied by Asada Iron Works. Co., LTD. is preferably used.

As shown in Fig. 1, the continuous kneader 10 has a basic structure including a feeding portion 1, a kneading portion 2, a discharge portion 3, and a metering feeder portion 4. The feeding portion 1 includes a cylindrical outer casing 11 extending in the horizontal direction and a screw shaft 12 concentric with the outer casing 11 and assembled in a sliding contact state. A raw material inlet 111 for receiving a raw material from the metering feeder portion 4 is opened on the top surface of the outer casing 11 on the upstream side. The starting end of the auger 12 (the right side of FIG. 1) is concentrically fixed to the drive shaft 121 (omitted in FIG. 1) of the drive motor, and the screw 12 is wound around the drive shaft via the medium of the drive shaft 121. The axis of the shaft 121 rotates. A spiral fin 122 formed in a predetermined direction is mounted on the outer surface of the auger 12. The material supplied from the metering feeder portion 4 is strongly supplied to the kneading portion 2 by the pivoting of the spiral fins 122.

The metering feeder portion 4 is installed for the raw material to be subjected to the continuous kneading treatment (in the present invention, an organic pigment, a water-soluble inorganic salt, a water-soluble organic liquid and a resin or an organic dye derivative, an anthracene derivative or the like) A sol or gel mixture of the derivative, sometimes referred to as "kneading composition" hereinafter, is supplied to the charging portion 1. The metering feeder portion 4 includes a raw material funnel 41 that supplies raw material, a screw feeder 42 that supplies raw material from the bottom of the raw material funnel 41 to the feeding portion 1, and a vertical mounting from the periphery of the raw material inlet 111 in the outer casing 11 to cover the spiral The connecting cylinder 43 at the outlet end of the feeder 42.

The auger 42 is mounted such that its helical fins are in sliding contact with the intermediate cylinder 44, which is mounted between the bottom opening of the material funnel 41 and the upper opening of the connecting cylinder 43. The starting end of the auger 42 (right side of Fig. 1) is concentrically coupled to the drive shaft of the feed motor omitted in Fig. 1. Therefore, by means of the pivoting of the screw feeder 42 by the driving of the feed motor, the material in the material hopper 41 is conveyed by the screw feeder 42 through the intermediate cylinder 44 and the connecting cylinder 43 by a predetermined amount of conveyance. Into the outer casing 11.

The kneading portion 2 includes a plurality of fixed disks 21, an annular kneading cylinder 22 mounted between the fixed disks 21, and a rotary disk 23, and the fixed disk 21 and the annular kneading cylinder 22 are alternately arranged to rotate the front and rear surfaces of the disk 23. (The right surface and the left surface in Fig. 1) are opposed to the fixed disk 21 and are fitted concentrically into the kneading cylinder 22. The tie rod omitted in FIG. 1 is inserted through the above-described plurality of fixed disks 21 and kneading cylinders 22. The fixed end of the tie rod is fixed to the outer casing 11 of the feeding portion 1. Thus, the fixed disk 21 and the kneading cylinder 22 are combined with the feeding portion 1.

Each of the rotary disks 23 is fitted in a pin groove shaft (omitted in FIG. 1) which projects concentrically from the foremost surface of the auger 12. A cylindrical intermediate screw 24 is mounted between each two adjacent rotating disks 23. Thus, the rotary disk 23 and the screw 24 are alternately mounted on the pin groove shaft. The outer diameter of the rotary disk 23 is slightly smaller than the inner diameter of the kneading cylinder 22, and the outer diameter of the intermediate screw 24 is slightly smaller than the inner diameter of the fixed disk 21. For this reason, in the case where the rotary disk 23 and the intermediate screw 24 are alternately fitted on the pin groove shaft, the outer circumferential surfaces of the respective rotary disks 23 and the respective intermediate screws 24 pass through the gap through which the raw material can pass, respectively, and the kneading cylinder 22 and fixed. The inner circumferential surfaces of the disks 21 are opposed to each other.

Due to the above configuration of the continuous kneading machine 10, the raw material in the raw material funnel 41 is taken out from the bottom of the raw material funnel 41 by the driving of the screw feeder 42, and then introduced into the charging portion 1 through the intermediate cylinder 44 and the connecting cylinder 43. In the outer casing 11. The raw material introduced into the outer casing 11 is continuously conveyed to the kneading portion 2 on the downstream side by the rotation of the spiral fin 122 due to the driving rotation of the auger 12.

Then, the raw material conveyed to the kneading portion 2 is first passed through the gap between the outer circumferential surface of the intermediate screw 24 which is pivoted about the most upstream side (the right side in FIG. 1) and the inner circumferential surface of the most upstream side fixed disk 21. . Then, the raw material passes through the gap between the left side surface of the fixed disk 21 on the most upstream side in FIG. 1 and the right side surface of the rotary disk 23 which is pivoted about the most upstream side. When the raw material passes through these gaps, the raw material is kneaded. The above operation of the raw material is repeated in a plurality of stages in accordance with the number of the fixed disk 21, the kneading cylinder 22, the rotary disk 23, and the intermediate screw 24 installed. For this reason, various components of the raw material (organic pigment, water-soluble inorganic salt and water-soluble organic liquid and resin or organic dye derivative, anthraquinone derivative or three in the present invention) The derivative) is subjected to a kneading treatment. The product obtained by the completion of the kneading process is discharged from the gap, that is, the discharge portion 3, between the outer circumferential surface of the rotary disk 23 on the most downstream side and the inner circumferential surface of the kneading cylinder 22 on the most downstream side.

Fig. 2 shows a front view (viewed from the right side of Fig. 1) or a rear view (viewed from the left side of Fig. 1) for the fixed and rotating disks of the continuous kneading specific example shown in Fig. 1. In Fig. 2, (a) is a cavity sector-shaped fixed disk 21a, (b) is a cavity sector-shaped rotating disk 23b, (c) is a cavity rose-shaped fixed disk 21c, and (d) is a cavity rose-shaped rotating disk 23d. (e) is a cavity-shaped fixed disk 21e, and (f) is a cavity-shaped rotating disk 23f.

As shown in Fig. 2, each of the fixed disks 21 has a movable fitting hole 211 concentric with the intermediate screw 24, wherein the intermediate screw 24 will be loosely fitted. In the radial direction of the movable fitting hole 211, a plurality of recesses (cavities (crushing spaces) 212) are formed hollow on the front and rear surfaces (front side and rear side) of each of the fixed disks 21, in the circumferential direction These notches are provided at regular intervals. On the other hand, each of the rotary disks 23 has a fitting hole 231 concentric with the pin groove shaft, in which the bolt groove shaft omitted in Fig. 1 is assembled in close contact. A cavity (shredding space) 232 corresponding to the cavity 212 of the fixed disk 21 is formed hollow on the front and rear surfaces of the respective rotary disks 23. The edges of the respective cavities 232 of the rotary disk 23 are open.

Due to the driving of the auger 12, the material introduced into the gap between the fixed disk 21 and the rotary disk 23 is continuously advanced into the respective cavities 212 and 232. In this state, the rotating disk 23 that rotates about the axis at the interface of the cavities 212 and 232 creates a shearing force on the raw materials in the cavities 212 and 232. That is, the ridge portions of the cavities 212 and 232 partially cut apart the cavities 212 of the fixed disk 21 and the cavities 232 of the rotating disk 23, thereby generating shearing force on the material and replacing it. The raw material is kneaded and dispersed. During the above replacement process, the sheared material exits the cavities 212 and 232 and the new material enters the same cavity 212 and 232.

Depending on the shape of the cavities 212 and 232, the fixed disk 21 and the rotating disk 23 are divided into a plurality of different kinds of fixed disks and rotating disks. That is, they respectively enter the cavity sector-shaped fixed disk 21a and the cavity sector-shaped rotating disk 23b shown in (a) and (b) of Fig. 2, and the cavities shown in (b) and (c) of Fig. 2, respectively. A rose-shaped fixed disk 21c and a cavity rose-shaped rotating disk 23d, and a cavity-shaped fixed disk 21e and a cavity-shaped rotating disk 23f shown in (e) and (f) of Fig. 2 are provided. These different kinds of fixed discs and rotating discs are used to increase the shearing force acting on the raw material according to the progress of the kneading and dispersing treatment.

That is, from highest to lowest, the order of the void ratio of the cavity 212 or 232 (the area of the cavity 212 of the fixed disk 21 or the cavity 232 of the rotating disk 23 is based on the percentage of the surface area of the fixed disk 21 or the rotating disk 23 ( %)) is a sectored cavity 212 or 232, a rose shaped cavity 212 or 232, and a dome shaped cavity 212 and 232. The shearing force acting on the raw material increases as the void ratio decreases.

In this specific example, the fixed disk 21 having the sector-shaped cavity 212 and the rotary disk 23 having the sector-shaped cavity 232, the fixed disk 21 having the rose-shaped cavity 212, and the rose-shaped cavity are sequentially disposed from the upstream side to the downstream side. A rotary disk 23 of 232; and a fixed disk 21 having a dome-shaped cavity 212 and a rotary disk 23 having a dome-shaped cavity 232 to increase the shearing force acting on the raw material according to the progress of kneading and dispersing the raw material.

Thus, the large shear force is not suddenly applied to the raw material, but the shearing force acting on the raw material is continuously increased as the kneading and dispersing treatment of the raw material proceeds. Therefore, the kneading and dispersion treatment is smoothly applied to the raw material without any additional strain. Thus, it is possible to make organic pigments, water-soluble inorganic salts, water-soluble organic liquids and resins or organic dye derivatives, anthracene derivatives or three which are all raw material components. The derivatives are successfully kneaded and dispersed with each other.

According to the continuous kneader 10 having such a structure, when the organic pigment as a raw material component is composed of coarse particles, by introducing the organic pigment into the gap between the fixed disk 21 and the rotary disk 23 (in particular, the cavity 212 and In 232), a shear force is applied to the coarse particles by the rotation of the rotary disk 23, whereby the coarse particles of the organic pigment can be pulverized into fine particles.

On the other hand, when the organic pigment is composed of aggregates of fine particles, by introducing these aggregates into the gap between the fixed disk 21 and the rotary disk 23 (particularly, the cavities 212 and 232) and rotating the rotary disk 23 It is capable of stably cracking and homogenizing these aggregates.

The pigment kneaded and dispersed by the above-described continuous kneader 10 will be described in detail below. The pigment composition of the present invention 1 is obtained by kneading a mixture comprising an organic pigment, a water-soluble inorganic salt, a water-soluble organic liquid and a resin by a continuous kneader 10, and the continuous kneading machine 10 includes a transmission shaft 121, an annular fixing plate 21, and a fixing The disk 21 is concentric and rotates entirely around the axis of the drive shaft 121, and a pulverizing space formed in the gap between the fixed disk 21 and the rotary disk 23.

The organic pigment used in the present invention refers to an organic pigment which is selected to have appropriate reaction conditions during synthesis to make the particle size fine and uniform, such as an azo pigment; in the post-treatment, the synthesis of agglomerated extremely fine particles An organic pigment which is capable of making its particle size uniform, such as a polyhalogenated copper indigo pigment; and an organic pigment capable of uniformizing the size of coarse particles and uneven particles produced in its synthesis by finely divided particles in a post-treatment. Such as copper phthalocyanine pigment. Further, the organic pigment is not particularly limited in structure as long as it is a pigment which requires finely divided and uniform in size. The organic pigment may be selected from conventional organic pigments. Examples of the organic pigment include azo pigment, indigo pigment, and quinophthalone pigment, and also include isoindolinone, isoporphyrin, perylene, anthrone, diketopyrrolopyrrole, thioindigo, and , quinolones, hydrazine and hydrazine. The mixture of at least two organic pigments can be finely pulverized.

The water-soluble inorganic salt used in the present invention is not particularly limited. Examples thereof include table salt (sodium chloride), potassium chloride, sodium sulfate, zinc chloride, calcium chloride, and mixtures thereof.

The water-soluble organic liquid used in the present invention is added to form a uniform slurry of the organic pigment and the water-soluble inorganic salt. The water-soluble organic liquid is not particularly limited as long as it can be freely mixed with water, or even if it cannot be freely mixed with water, has solubility which can be removed by industrial water washing, and it also allows the pigment particles to grow. The liquid tends to evaporate easily due to an increase in temperature during kneading. For this reason, it is preferred to use a high boiling point solvent in view of safety. For example, it includes 2-(methoxy)ethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, and diethylene glycol. Ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy 2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low molecular weight polypropylene glycol, aniline, pyridine, tetrahydrofuran, dioxane , methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, propylene glycol, propylene glycol monomethyl ether acetate, ethyl acetate, isopropyl acetate, acetone, methyl ethyl ketone, dimethyl Carbenamide, dimethyl hydrazine and N-methylpyrrolidone. A mixture of at least two organic liquids can be used as needed.

The resin used in the present invention is preferably a resin which is hardly soluble in water, liquid or solid at room temperature, and partially soluble in the water-soluble organic liquid used in the present invention. Examples include rosin resins such as rosin, disproportionated rosin, polymerized rosin, hydrogenated rosin, rosin ester, rosin amine, maleic acid modified rosin, fumaric acid modified rosin, rosin metal salt, rosin modified phenolic resin, and rosin modified horse. Acid resin, synthetic resin such as epoxy resin, acrylic resin, maleic acid resin, butyral resin, polyester resin, melamine resin, phenolic resin, polyurethane resin and polyamide resin, and derived from cellulose, rubber, etc. Modified resin. In particular, rosin resins are preferred in view of the added effect and price.

The amount of the water-soluble inorganic salt in the kneaded composition of the present invention is not particularly limited. The amount of the water-soluble inorganic salt is preferably from 0.5 to 30 times by weight based on the amount of the organic pigment. When it is less than 0.5 weight times, fine crushing is difficult. When it is more than 30 times by weight, it is possible to obtain finely divided pigments, but the amount of the pigment to be processed becomes smaller, so that the productivity is disadvantageously lowered industrially.

The amount of the water-soluble organic liquid in the kneaded composition of the present invention is not particularly limited. The amount of the water-soluble organic liquid is preferably from 0.01 to 0.5 times by weight based on the total amount of the organic pigment and the water-soluble inorganic salt. When it is less than 0.01 by weight, the kneaded composition becomes too hard to be stably handled. When it is 0.5 times by weight, the kneaded composition becomes too soft so that the degree of fine crushing is lowered.

Further, the amount of the resin in the kneaded composition of the present invention is not particularly limited. The amount of the resin is preferably from 0.001 to 1.0 times the weight of the organic pigment. When the weight is less than 0.001 times, the effect of addition cannot be achieved. When the weight is more than 1.0 times, the effect corresponding to the amount of addition of the resin cannot be achieved. Further, it is preferred to control the amount of the resin depending on the difference in properties of the resin and the vehicle resin used in the obtained pigment composition. That is, when the difference is large, the resin is used in a minimum amount to reduce the influence on the physical properties of the vehicle resin. On the other hand, when the difference is small, the amount of the resin is preferably increased to sufficiently exhibit the effects of the present invention.

The organic pigment, the water-soluble inorganic salt, the water-soluble organic liquid, and the resin which are components of the kneading composition of the present invention can be simultaneously added to a continuous kneader, respectively. Additionally, these components can be added to the continuous kneader after mixing. Further, it is also possible to add a resin in the process of preparing the organic pigment to preliminarily form a mixture of the organic pigment and the resin. In this case, the effect of adding the resin is remarkably exhibited.

The present invention 2 relates to a method of preparing a pigment composition, which comprises kneading an organic dye derivative, an anthracene derivative or the like by a continuous kneader a mixture of a derivative, an organic pigment, a water-soluble inorganic salt and a water-soluble organic liquid, each of the above derivatives having at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group. The above continuous kneader includes a drive shaft, an annular fixed disk, a rotary disk that is concentric with the fixed disk and that rotates around the shaft of the drive shaft, and a pulverizing space formed in a gap between the fixed disk and the rotary disk.

The organic dye derivative containing at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group in the invention 2 is typically represented by the following formula (1). Organic dye derivative, P-{X ₁ -(Y ₁ )k}m (1)

Wherein P represents an organic dye residue; X ₁ is a single bond or represents -O-, -S-, -CO-, -SO ₂ -, -NR ₁ -, -CONR ₁ -, -SO ₂ NR ₁ -, - NR ₁ CO- or NR ₁ SO ₂ -, a linear or branched alkylene group having 1 to 12 carbon atoms, a benzene or a triyl group which may be substituted by an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group or a halogen atom a residue, or a linking group consisting of at least two of these linking groups, wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; Y ₁ is a quinone imine group which may be substituted by a nitro group or a halogen atom Methyl, -NR ₂ R ₃ , -SO ₃ . M/n or -COO. M/n; wherein R ₂ and R ₃ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted phenyl group, or R ₂ and R ₃ together form a substitution Or an unsubstituted heterocyclic ring which may contain an additional nitrogen atom, an oxygen atom or a sulfur atom, M represents a hydrogen ion, a metal ion having a valence of 1 to 3 or an ammonium ion substituted by at least one alkyl group, and n is M The valence; k is an integer of 1 or 2; m is an integer from 1 to 4.

The anthracene derivative containing at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group used in the present invention 2 is typically represented by the following formula (2) Anthracene derivative, Q-{X ₂ -(Y ₂ )k}m (2)

Wherein Q represents an anthracene residue which may be substituted by an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group or a halogen atom; X ₂ is a single bond or represents -O-, -S-, -CO-, -SO ₂ -, -NR ₁ -, -CONR ₁ -, -SO ₂ NR ₁ -, -NR ₁ CO- or NR ₁ SO ₂ -, a linear or branched alkylene group having 1 to 12 carbon atoms, which may be alkane a benzene or a triyl group substituted with a amide group, an amine group, a nitro group, a hydroxyl group, an alkoxy group or a halogen atom a residue, or a linking group consisting of at least two of these linking groups, wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; and Y ₂ is a quinone imine group which may be substituted by a nitro group or a halogen atom Methyl, -NR ₂ R ₃ , -SO ₃ . M/n or -COO. M/n; wherein R ₂ and R ₃ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted phenyl group, or R ₂ and R ₃ together form a substitution Or an unsubstituted heterocyclic ring which may contain an additional nitrogen atom, an oxygen atom or a sulfur atom, M represents a hydrogen ion, a metal ion having a valence of 1 to 3 or an ammonium ion substituted by at least one alkyl group, and n is M The valence; k is an integer of 1 or 2; m is an integer from 1 to 4.

Three used in the present invention 2 containing at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group The derivative is typically an anthracene derivative represented by the following formula (3),

Where R represents three Residue; each of X ₃ -X ₅ is independently a single bond or represents -O-, -S-, -CO-, -SO ₂ -, -NR ₁ -, -CONR ₁ -, -SO ₂ NR ₁ -, -NR ₁ CO- or NR ₁ SO ₂ -, a linear or branched alkylene group having 1 to 12 carbon atoms, which may be substituted by an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group or a halogen atom a benzene residue, or a joint linking group consisting of at least two of these linking groups, wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; and Y ₃ is a fluorene which may be substituted by a nitro group or a halogen atom. Aminomethyl, -NR ₂ R ₃ , -SO ₃ . M/n or -COO. M/n; wherein R ₂ and R ₃ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted phenyl group, or R ₂ and R ₃ together form a substitution Or an unsubstituted heterocyclic ring which may contain an additional nitrogen atom, an oxygen atom or a sulfur atom, M represents a hydrogen ion, a metal ion having a valence of 1 to 3 or an ammonium ion substituted by at least one alkyl group, and n is M The valence of the formula; each of Y ₄ and Y ₅ independently has the same definition as the definition of Y ₃ or represents an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group, a halogen atom or a substituted or unsubstituted phenyl group; , q and r are each an integer of 1 or 2 independently.

Examples of the organic dye used in the organic dye derivative of the formula (1) of the present invention 2 include a diketopyrrolopyrrole dye, an azo dye such as an azo dye, a diazo dye and a polyazo dye, an indigo dye, and an anthraquinone dye. Dyes such as diamino hydrazine, fluorinated pyrimidine, flavonoid, ruthenium, guanidine, ketone and fluorenone violet, quinacridone dye, two Dyes, perinone dyes, perylene dyes, thioindigo dyes, isoporphyrin dyes, isoindolinone dyes, quinolone dyes, mineral dyes and metal complex dyes. The oxime of the oxime derivative of the formula (2) may be an alkyl group, an amine group, a nitro group, a hydroxyl group represented by a methyl group or an ethyl group, an amino group represented by a methyl group or an ethyl group, an alkoxy group represented by a methoxy group or an ethoxy group, Or a ruthenium of a halogen atom represented by chlorine. Formula (3) three Derivative three Is 1,3,5-three .

The organic dye derivative of the formula (1), the anthracene derivative of the formula (2) and the three formula (3) in the invention 2 Derivatives are introduced via the introduction of specific substituents to the above organic dyes, hydrazine or tris The organic compound obtained on it. Examples of the substituent include quinone iminomethyl, 4-nitroindenidomethyl, 4-chloroindenidomethyl, tetrachloroindenidomethyl, (4, 6 - bis(indenylaminomethyl)-1,3,5-three -2-ylaminomethyl, aminomethyl decyl, sulfonyl, methylamino, ethylamino, propylamino, butylamino, hexylamino, octylamino, dodecylamino, Octadecylamino, dimethylamino, diethylamino, dibutylamino, dimethylaminopropylamino, diethylaminopropylamino, diethylaminoethylamine, dibutylaminopropylamine, Acridine methyl, dimethylaminomethyl, diethylaminomethyl, dibutylaminomethyl, (4,6-bis(diethylaminopropylamino)-1,3,5-three )-2-yl, (4,6-bis(diethylaminopropylamino)-1,3,5-three )-2-ylamino, (4-(diethylaminopropylamino)-6-hydroxy-1,3,5-three -2-ylamino, dimethylaminopropylamine sulfonyl, diethylaminopropylamine sulfonyl, dibutylaminopropylamine sulfonyl, morpholinoethylamine sulfonyl, dimethylaminopropyl carbonyl 4-(Diethylaminopropylamine carbonyl)anilinocarbonyl, dimethylaminomethylcarbonylamine methyl, diethylaminopropylamine methylcarbonylaminemethyl, dibutylamine propylamine methylcarbonylaminemethyl , sulfonic acid group, sodium sulfonate group, calcium sulfonate group, sulfonate sulfonate group, sulfonate sulfonate group, aluminum sulfonate group, 4-(sulfonic acid aluminum) phenylamine decylmethyl group, dodecane Aminosulfonic acid group, octadecylaminosulfonic acid group, trimethyloctadecylaminosulfonic acid group, dimethyldidecylaminosulfonic acid group, carboxylic acid group and 2-carboxylic acid Aluminum-5-nitrobenzimidylmethyl. For the three of formula (3) The derivative, in addition to the above substituents, examples of the substituent include a hydroxyl group, an amine group, a methoxy group, an ethoxy group, a phenoxy group, a 4-nitroanilino group, a 4-anilinoanilide group or a 4-amino group. Phenoxy.

The organic dye derivative of the formula (1), the anthracene derivative of the formula (2) and the three formula (3) in the invention 2 The derivative can be disclosed, for example, by JP-B-39-28884, JP-A-51-18736, JP-A-54-62227, JP-A-56-32549, JP-A-56-81371, JP-A. -56-118462, JP-A-56-166266, JP-A-59-96175, JP-A-60-88185, JP-A-60-98525, JP-A-63-305173, JP-A-03 Prepared by the method of -26767 and JP-A-11-199796.

The organic dye derivative of the formula (1), the anthracene derivative of the formula (2) and the three formula (3) in the invention 2 A specific example of the derivative is shown by the compound number as follows.

An organic dye derivative selected from the group consisting of (1), an anthracene derivative of the formula (2), and three of the formula (3) Each of the organic compound of the derivative, the organic pigment, the water-soluble inorganic salt, and the water-soluble organic liquid is a component of the kneaded composition of the present invention 2, which can be simultaneously independently added to the continuous kneader. Additionally, these components can be added to the continuous kneader after mixing. Further, it is also possible to add the above derivative in the process of preparing an organic pigment to preliminarily form a mixture of an organic pigment and a derivative. In this case, the effect of addition of the derivative is remarkably exhibited.

The operating conditions of the continuous kneader of the present invention are not particularly limited. In order to control the amount of treatment of the organic pigment or the quality of the obtained fine organic pigment, it is possible to adjust the kneading temperature and the input amount of mechanical energy (the number of revolutions of the main shaft (the transmission shaft 121), the supply amount of the raw material, the dynamic load of the main shaft, and the like). . For the grinding of organic pigment particles and the growth of organic pigment particles due to their contact with a water-soluble organic liquid, and for the effective progress of absorbing the resin onto the surface of the organic pigment by dissolving the resin in a water-soluble organic liquid, kneading The temperature is preferably from 10 to 150 ° C, particularly preferably from 40 to 130 ° C. An increase in the kneading temperature can promote the growth rate of the pigment particles. The treatment amount or mass of the pigment composition can be adjusted by adjusting the mixing ratio of the kneading composition, the kneading temperature, and the input amount of mechanical energy (the number of revolutions of the main shaft (the transmission shaft 121), the supply amount of the raw material, the dynamic load of the main shaft, and the like). control. When the kneading temperature is higher than 150 ° C, the particle growth is considerable, so that kneading is required in a short time. However, in this case, the time for particle homogenization becomes shorter, which is not preferable in view of quality. After the kneading starts, heat or cool as needed. Further, it is possible to change the mixing ratio of the kneaded composition by providing the raw material inlet at the intermediate position of the continuous kneader and adding the resin, the derivative or the water-soluble organic liquid in the continuous kneading step. It is also possible to adjust the entire kneading condition by connecting a plurality of continuous kneaders in series and adjusting the operating conditions of the respective continuous kneaders differently.

The kneaded pigment composition is treated according to a usual method. That is, the kneaded composition is treated with water or an aqueous solution of an inorganic acid, then filtered and washed with water to remove the water-soluble inorganic salt and the water-soluble organic liquid and separate the pigment composition. The pigment composition in a wet state can be used directly. Further, a powdery pigment composition obtained by drying and pulverization can also be used. Resins, surfactants, and/or other additives may be added after kneading as needed.

The average primary particle diameter of the fine organic pigment varies depending on the conditions of the finely divided treatment and the kind of the organic pigment. The original particle diameter can be arbitrarily controlled in the range of about 10 to 500 nm by appropriately adjusting the conditions.

In the pigment composition of the present invention, extremely fine pigment particles are prepared with a small amount of energy by means of a special continuous kneader. In order to enable the pigment composition to be dispersed in the ink or the coating while maintaining the fine pigment particles, the pigment particles are coated with the resin or the derivative by the addition of the resin or the derivative in the kneading step, thereby reducing mutual agglomeration of the pigment particles, At the same time, finely divided pigment particles are maintained. The pigment composition of the present invention is suitable for applications requiring high transparency. Therefore, the pigment composition of the present invention exhibits particularly excellent quality in applications such as gravure inks, inkjet inks, and color filters. In addition, it exhibits excellent quality in applications such as offset inks, coatings, plastic coloring and color toners. For example, when preparing a gravure ink, the vehicle used is composed of a resin and a solvent. The vehicle is not particularly limited and may contain an auxiliary agent or an extender pigment. Examples of the resin include rosin, wood steamed rosin, tall oil rosin, lime rosin, rosin ester, maleic acid resin, polyamide resin, vinyl resin, nitrocellulose, cellulose acetate, ethyl cellulose, chlorination Rubber, cyclized rubber, ethylene-vinyl acetate copolymer resin, urethane resin, polyester resin, alkyd resin, acrylic resin, black pitch, Dama resin, shellac, resin mixture containing the above resin, by any one The above resin mixture and the water-soluble resin obtained by dissolving the above resin in water, and an emulsified resin. Solvents include, for example, hydrocarbons, alcohols, ketones, ether alcohols, ethers, esters, and water. In particular, when a cellulose-based resin is used, a high-quality gravure ink having good transparency, high gloss, and high definition can be obtained. Further, the pigment composition is excellently mixed with the vehicle by using a dispersing device such as a dissolver, a high-speed mixer, a homomixer, a kneader, a rinsing device, a roll crusher, a sand mill or an attritor. It is dispersed in the vehicle.

The coloring composition for a color filter provided by the present invention 3 is a coloring composition for a color filter comprising a pigment carrier and a pigment composed of a transparent resin, a precursor thereof or a mixture thereof, and the coloring composition is characterized in that The pigment comprises a fine organic pigment obtained by kneading a mixture comprising an organic pigment, a water-soluble inorganic salt and a water-soluble organic liquid by a continuous kneader, the continuous kneader comprising a drive shaft, an annular fixing plate, concentric with the fixing plate and the entire winding shaft The rotating disk of the shaft is rotated, and the pulverizing space formed in the gap between the fixed disk and the rotating disk.

Further, the color filter of the present invention 3 is characterized in that the color filter comprises a color filter sheet formed of the coloring composition of the present invention.

Then, a mixture containing an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid and optionally a resin and/or a pigment derivative to be subjected to kneading by the continuous kneader 10 will be described in detail (hereinafter sometimes referred to as "kneading" Composition").

The organic pigment used in the present invention 3 is selected from known organic pigments for color filters. The organic pigments may be used singly or in combination. When an organic pigment having an average primary particle diameter of 0.1 to 0.5 μm is used as the organic pigment, the organic pigment can be finely pulverized into extremely fine particles having an average primary particle diameter of 0.01 to 0.1 μm and exhibiting a particularly high Contrast, so it is preferred to use this organic pigment. As the organic pigment, a crude organic pigment whose state is not changed by its synthesis can also be used, that is, (a) a large particle having an average primary particle diameter of about 10 to 200 μm or (b) an average primary particle diameter can be used. Very strong agglomerated particles (aggregates) of very fine particles of 0.01 μm or less.

A specific example of the organic pigment which can be used in the present invention 3 is explained below using a chromaticity index.

For the red coloring composition used to form the red color filter sheet, red pigments such as CI Pigment Red 7, 9, 14, 41, 48:1, 48:2, 48:3, 48:4, 81:1 can be used. , 81:2, 81:3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220 , 223, 224, 226, 227, 228, 240, 246, 254, 255, 264, and 272. In the red pigment composition, a yellow pigment and/or an orange pigment may be additionally used.

For the yellow colored composition for forming a yellow color filter sheet, a yellow pigment such as CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18 can be used. , 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73 , 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120 ,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194 and 199.

For the orange coloring composition for forming the orange color filter sheet, orange pigments such as C.I. Pigment Oranges 36, 43, 51, 55, 59, and 61 can be used.

For the green coloring composition for forming a green color filter sheet, green pigments such as C.I. Pigment Green 7, 10, 36 and 37 can be used. In the green coloring composition, a yellow pigment may be additionally used.

For the blue coloring composition used to form the blue color filter sheet, a blue pigment such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, may be used. 22, 60 and 64. In the blue coloring composition, a purple pigment such as C.I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42 and 50 may be additionally used.

For the cyan coloring composition for forming a cyan color filter sheet, blue pigments such as C.I. Pigment Blue 15:1, 15:2, 15:4, 15:3, 15:6, 16 and 81 can be used.

For the magenta colored composition for forming the magenta color filter sheet, a violet pigment and a red pigment such as C.I. Pigment Violet 1 and 19 and C.I. Pigment Red Red 144, 146, 177, 169 and 81 can be used. In the magenta colored composition, a yellow pigment may be additionally used.

When kneading a mixture of an organic pigment, a water-soluble inorganic salt, and a water-soluble organic liquid, in order to prevent crystal growth or crystal transformation of the organic pigment, it may be added by introducing a basic or acidic substituent or a guanidinomethyl group to the organic Pigment, hydrazine, acridone or three Derivatives obtained in . In particular, a pigment derivative obtained by introducing a basic or acidic substituent or a quinone iminomethyl group into an organic pigment is preferably added. As the basic substituent, a substituent represented by the following formulas (4) to (7) can be used. The acidic substituent is typically a sulfonic acid group or a carboxyl group.

A pigment derivative having the same matrix structure as the finely divided organic pigment is preferred as the pigment derivative. Pigment derivatives having a different matrix structure than finely divided organic pigments can also be used.

The amount of the pigment derivative used per 1 part by weight of the organic pigment in the kneaded composition is preferably from 0.001 part by weight to 0.3 part by weight. When the amount of the pigment derivative is less than 0.001 parts by weight, it is difficult to achieve an additive effect. When the amount of the pigment derivative is more than 0.3 parts by weight, the effect corresponding to the added amount cannot be attained, and further, the obtained fine organic pigment is made into a mixture of a pigment and a pigment derivative. In this case, the difference in physical properties of the organic pigment as a single substance becomes large, so that sometimes a color filter formed by using a colored composition containing such a fine organic pigment may have problems in actual quality. .

In the formulae (4) to (7), X represents -SO ₂ -, -CO-, -CH ₂ NHCOCH ₂ -, -CH ₂ - or a single bond; n represents an integer of 1 to 10; R ₁ and R ₂ Each independently represents a substituted or unsubstituted alkyl group having 1 to 36 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 36 carbon atoms or a substituted or unsubstituted phenyl group, or R ₁ and R ₂ together form a substituted or unsubstituted heterocyclic ring, which may also contain a nitrogen atom, an oxygen atom or a sulfur atom; R ₃ represents a substituted or unsubstituted alkyl group having 1 to 36 carbon atoms, having 2 to 36 a substituted or unsubstituted alkenyl group of a carbon atom or a substituted or unsubstituted phenyl group; each of R ₄ , R ₅ , R ₆ and R ₇ independently represents a hydrogen atom, a substituted or unsubstituted having 1 to 36 carbon atoms An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 36 carbon atoms or a substituted or unsubstituted phenyl group; Y represents -NR ₈ -Z-NR ₉ - or a single bond, wherein R ₈ and R _{9 are} each a substituted or unsubstituted alkyl group independently having a hydrogen atom, having 1 to 36 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 36 carbon atoms, or a substituted or unsubstituted a group; Z represents a substituted or unsubstituted alkylene group having 1 to 36 carbon atoms, a substituted or unsubstituted olefinic group having 2 to 36 carbon atoms or a substituted or unsubstituted phenylene group; a substituent represented by the formula (8),

Wherein n, R ₁ and R ₂ are as defined above, or a substituent represented by the formula (9),

Wherein R ₃ to R ₇ are as defined above; and Q represents a hydroxyl group, an alkoxy group, a substituent represented by the above formula (8) or a substituent represented by the above formula (9).

Examples of the organic pigment constituting the pigment derivative include a diketopyrrolopyrrole dye; an azo dye such as azo; a diazo or polyazo dye; an indigo dye; an anthraquinone dye such as a diamine-linked anthracene, a purine-pyrimidine , yellow ketone, sputum, sputum, scorpion ketone or fluorenone purple; quinacridone dye; Dye; anthrone dye; perylene dye; thioindigo dye; isoporphyrin dye; isoindolinone dye; quinolone dye; Shilin dye and metal complex dye. Further, the pigment used in the kneading composition described above can be used.

The anthracene and acridone which respectively constitute an anthracene derivative and an acridone derivative are each an alkyl group, an amine group, a nitro group, a hydroxyl group, and a methoxy group which may each have a substituent such as a methyl group or an ethyl group. An alkoxy group represented by a ethoxy group or an oxime and an acridone represented by a halogen.

Composition three Derivative three Is 1,3,5-three which can have the following substituents , for example, an alkyl group represented by a methyl group or an ethyl group; an amine group or an alkylamino group represented by a dimethylamino group, a diethylamino group or a dibutylamine group; a nitro group, a hydroxyl group, a methoxy group, an ethoxy group Or an alkoxy group represented by a butoxy group; a halogen represented by chlorine, a phenyl group which may be substituted by a methyl group, a methoxy group, an amine group, a dimethylamino group or a hydroxyl group; or may be a methyl group, an ethyl group, a methoxy group An anilino group substituted with a ethoxy group, an amine group, a dimethylamino group, a diethylamino group, a nitro group or a hydroxy group.

Pigment derivatives, anthracene derivatives and acridone derivatives each having a basic substituent can be synthesized by various synthetic routes. For example, they can be obtained by introducing a substituent represented by any one of the following formulas (10) to (13) into an organic pigment, hydrazine or acridone such that the substituent can react with the above substituent The amine component reacts to form a substituent represented by any one of the formulae (4) to (7). Examples of the amine component include N,N-dimethylaminopropylamine, N-methyloxime , diethylamine and 4-[4-hydroxy-6-[3-(dibutylamino)propylamino]-1,3,5-three Alkyl-2-ylamino]aniline.

-SO ₂ Cl (10) -COCl (11) -CH ₂ NHCOCH ₂ Cl (12) -CH ₂ Cl (13)

In the reaction of the substituent represented by any one of the formulae (10) to (13) with the above amine component, a substance formed by the hydrolyzed moiety of any of the substituents of the formula (10) to (13) and a hydroxyl group can be simultaneously present. A substance formed by replacing a chlorine atom. In this case, the substituent of the formula (10) is a sulfonic acid group and the substituent of the formula (11) is a carboxylic acid group. Each of them can be a free acid. Further, each of them may be a salt having a valence of 1 to 3 or a salt of the above monoamine.

When the organic pigment is an azo pigment, a base having a basic group can be prepared by introducing a substituent represented by any one of the formulae (4) to (7) into a diazo component or a coupling component in advance, followed by coupling reaction. Azo pigment derivative.

In addition, three with a special basic group Derivatives can be obtained by various synthetic routes. For example, it can be synthesized by reacting at least one chlorine of cyanuric chloride as a starting material with an amine component, and then reacting residual chlorine of cyanuric chloride with an amine, an alcohol or the like, and reacting the above with an amine component. A substituent represented by any one of the formulae (4) to (7) such as N,N-dimethylaminopropylamine or N-methyloxime is formed. .

Specific examples of derivatives having a basic substituent are described below, however, the derivatives are not limited by these examples. These derivatives may be used singly or in combination.

Then, a coloring composition for a color filter provided by the present invention, which contains the fine organic pigment and the pigment carrier thus obtained, will be explained.

The fine organic pigment is dispersed in a pigment carrier contained in the colored composition of the present invention. The pigment carrier consists of a transparent resin, its precursor or a mixture thereof. The transparent resin exhibits a light transmittance of preferably 80% or more, more preferably 95% or more, over the entire visible wavelength of 400 to 700 nm. The transparent resin includes a thermoplastic resin, a thermosetting resin, and an active energy beam curable resin. Its precursors include monomers and oligomers each cured by irradiation with an active energy beam and thereby preparing a transparent resin. These can be used alone or in combination.

In the coloring composition, 30 to 700 parts by weight, preferably 60 to 450 parts by weight, of the pigment carrier may be used per 100 parts by weight of the pigment. When a mixture of a transparent resin and a precursor thereof is used as a pigment carrier, 20 to 400 parts by weight, preferably 50 to 250 parts by weight, of the transparent resin may be used per 100 parts by weight of the pigment in the coloring composition. Further, in the colored composition, 10 to 300 parts by weight, preferably 10 to 200 parts by weight, of the precursor of the transparent resin may be used per 100 parts by weight of the pigment.

Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, poly Ester resin, acrylic resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, cellulose, polyethylene (HDPE and LDPE), polybutadiene, and polyimide resin. Examples of the thermosetting resin include an epoxy resin, a benzoguanamine resin, a rosin-modified maleic acid resin, a rosin-modified fumaric acid resin, a melamine resin, a urea resin, and a phenol resin.

Examples of the active energy beam curable resin include: photoreaction by a reaction between a (meth)acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group, or a cinnamic acid and the above polymer A resin obtained by introducing a crosslinking group such as a (meth)acrylonitrile group or a styryl group into a polymer having a reactive substituent such as a hydroxyl group, a carbonyl group or an amine group, and a linear polymer such as styrene containing an acid anhydride. A resin prepared by semi-esterification of a maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer with a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth) acrylate.

Examples of the monomers and oligomers which are precursors of the transparent resin include various acrylates and methacrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, and 2-hydroxyethyl (meth)acrylate. a base ester, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1, 6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, Pentaerythritol tris(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol Epoxy glyceryl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tricyclodecenyl (meth)acrylate, ester acrylate, methyl (meth) acrylate of methylol melamine , epoxy (meth) acrylate and urethane acrylate; (meth) acrylate, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, penta Trivinyl ether alcohols, (meth) acrylamide, N- methylol (meth) acrylamide, N- vinyl formamide Amides and acrylonitrile. These can be used alone or in combination.

When the colored composition is cured by ultraviolet irradiation, a photopolymerization initiator or the like is added to the colored composition for a color filter of the present invention.

Examples of the photopolymerization initiator include an acetophenone photopolymerization initiator such as 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, and 1 -(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl benzophenone, 2-benzyl-2-dimethylamino-1-(4 -morpholinophenyl)-butan-1-one and 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one; benzoin photopolymerization Initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzyl dimethyl ketal; benzophenone photopolymerization initiators such as benzophenone, benzo Benzoic acid, methyl benzoylbenzate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone and 4-benzylidene-4 '-Methyldiphenyl sulfide; thioxanthone photopolymerization initiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone and 2,4-diiso Propyl thioxanthone; three Photopolymerization initiator such as 2,4,6-trichloro-s-three 2-phenyl-4,6-bis(trichloromethyl)-s-three , 2-(p-methoxyphenyl)-4,6-bis-(trichloromethyl)-s-three , 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-three , 2-piperidin-4,6-bis(trichloromethyl)-s-three 2,4-bis(trichloromethyl)-6-styryl-s-three , 2-(naphthoquinone-1-yl)-4,6-bis(trichloromethyl)-s-three , 2-(4-methoxy-naphthoquinone-1-yl)-4,6-bis(trichloromethyl)-s-three 2,4-trichloromethyl-(piperidinyl)-6-three And 2,4-trichloromethyl (4'-methoxystyryl)-6-three a borate photopolymerization initiator, a carbazole photopolymerization initiator, and an imidazole photopolymerization initiator. In the coloring composition, 5 to 200 parts by weight, preferably 10 to 150 parts by weight, of the photopolymerization initiator may be used per 100 parts by weight of the pigment.

The above photopolymerization initiators may be used singly or in combination. A compound which is a sensitizer such as α-decyloxyester, decylphosphine oxide, methylphenylglyoxylic acid, benzyl-9,10-phenanthrenequinone, anthrone oxime, ethyl hydrazine, 4 may be additionally used. , 4'-diethylisodiphenylphenolate, 3,3',4,4'-tetrakis(t-butylperoxycarbonyl)benzophenone and 4,4'-diethylaminobenzonitrile ketone. In the coloring composition, 0.1 to 60 parts by weight of a sensitizer may be used per 100 parts by weight of the photopolymerization initiator.

The colored composition for a color filter of the present invention 3 can be prepared in the form of a solvent development type or an alkali development type coloring resist. In the colored resist, the pigment is dispersed in a pigment carrier including a thermoplastic resin, a thermosetting resin or an active energy beam curable resin and a monomer. Dispersing one or at least two fine organic pigments together with a desired photopolymerization initiator by using a dispersing device such as a three-roll mill, a two-roll mill, a sand mill, a kneader or an attritor The colored resist is prepared by going to a pigment carrier. Further, the coloring composition for a color filter provided by the present invention can also be prepared by separately dispersing at least two kinds of the above fine pigments in a pigment carrier to prepare a dispersion, and then mixing the dispersion.

When the pigment is dispersed in the pigment carrier, a dispersing aid such as a resin-based pigment dispersant, a surfactant, the aforementioned pigment derivative, an anthracene derivative, an acridone derivative or the like may be used as needed. derivative. Since the dispersing aid can disperse the pigment excellently and has a good effect on preventing re-agglomeration of the pigment after dispersion, it is excellent when a coloring composition obtained by dispersing a pigment in a pigment carrier by using a dispersing aid is used. Transparency filter. In the colored composition, 0.1 to 40 parts by weight, preferably 0.1 to 30 parts by weight, of the dispersing aid may be used per 100 parts by weight of the pigment.

Among these dispersing aids, pigment derivatives, anthracene derivatives, acridone derivatives and three Derivatives (hereinafter sometimes referred to as "derivatives") are preferred dispersing aids because these derivatives have excellent functions for preventing agglomeration of fine organic pigments and keeping the organic pigment finely dispersed. And thus, a color filter having high contrast and high color purity can be prepared by using a colored composition containing at least one of these derivatives.

The resin-based pigment dispersant has a portion having affinity with the pigment and adsorbing on the pigment and a portion compatible with the pigment carrier, and its function is to stabilize the dispersion of the pigment in the pigment carrier by being absorbed on the pigment. The resin-based pigment dispersant specifically includes an oily dispersant such as a polyurethane, a polycarboxylate represented by a polyacrylate, an unsaturated polyamine, a polycarboxylic acid, a (partial) amine salt of a polycarboxylic acid, a polycarboxylic acid Ammonium salt, alkylamine salt of polycarboxylic acid, polyoxyalkylene oxide, long chain polyamine guanamine phosphate, ester of hydroxy group-containing polycarboxylic acid and its modified product, or by poly(lower alkylene) Amine, which is formed by reacting a polyester having a free carboxyl group, or a salt thereof; a water-soluble resin or a water-soluble polymer such as a (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(methyl) Acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or povidone; polyester; modified polyacrylate; ethylene oxide/propylene oxide and phosphate adduct. These resin-based pigment dispersants may be used singly or in combination.

Surfactants include anionic surfactants such as polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali metal salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonate, alkyl diphenyl ethers Sodium disulfonate, monoethanolamine lauryl sulfate, triethylamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, styrene-acrylic acid copolymer Ethanolamine and polyoxyethylene alkyl ether phosphate; nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, Polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate; cationic surfactants such as tetraalkylammonium salts and ethylene oxide adducts thereof; and amphoteric surfactants such as alkyl dimethicone Alkyl betaines represented by aminoacetic acid betaine, and alkyl imidazolines. These surfactants may be used singly or in combination.

In order to sufficiently disperse the pigment in the pigment carrier and to promote the formation of the color filter sheet by applying the coloring composition to a transparent substrate such as a glass substrate until the dry film thickness is 0.2 to 5 μm, the color filter provided by the present invention 3 is used for color filter The colored composition of the device may contain a solvent.

Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butanediol, 1,3-butanediol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, 3 -ethyl ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylacetate Ester, 3-methoxybutanol, 3-methoxyacetic acid butyl ester, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chloro Toluene, p-diethylbenzene, second butylbenzene, terphenylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, B Glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether Acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, B Alcohol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethylene ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl Ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol , cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol single Methyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol Monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, N-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate and dibasic acid esters. These solvents may be used singly or in combination. In the coloring composition, 800 to 4,000 parts by weight, preferably 1,000 to 2,500 parts by weight, per 100 parts by weight of the pigment may be used.

Further, the coloring composition for a color filter provided by the present invention 3 may contain a storage stabilizer for stabilizing the viscosity of the composition over time. Examples of storage stabilizers include tetraammonium chlorides such as benzyltrimethyl chloride and diethylhydroxylamine, organic acids such as lactic acid and oxalic acid and methyl ether thereof, tert-butyl catechol, and organic phosphines such as three Ethylphosphine and triphenylphosphine, and phosphite. In the coloring composition, 0.1 to 10 parts by weight of the storage stabilizer may be used per 100 parts by weight of the pigment.

The colored composition for a color filter provided by the present invention 3 may contain a dye for toning as long as the heat resistance is not lowered.

Preferably, 5 μ m or more, preferably 1 μm or more, more preferably 0.5 μm or more are removed from the colored composition of the present invention 3 by means of, for example, a centrifugal separator, a sintering screening program or a membrane screening program. The above coarse particles and mixed dust.

Next, the color filter of the present invention 3 will be explained.

The color filter of the present invention 3 comprises R (red), G (green), B (blue), Y (yellow), M (magenta) or C (cyan) formed on the surface of the transparent or reflective substrate. Color filter sheets of at least two colors. According to the printing method or the photolithography method, the color filter sheets of the respective colors can be formed by using the coloring composition for a color filter provided by the present invention. As the transparent substrate, a glass plate and a resin plate such as polycarbonate, methyl polymethacrylate, and polyethylene terephthalate can be used.

In the process of forming the respective color filter sheets according to the printing method, the coloring composition for the color filter prepared by repeating printing and drying as the above various printing inks can be patterned, and thus the printing method and the preparation filter The color method is a low cost method and is excellent in mass production. In addition, due to the development of printing technology, fine patterns with high dimensional accuracy and smoothness can be printed. For printing, it is preferred that the ink does not dry and solidify on a printing plate or blanket. Control of ink flow on the press is also important, and the viscosity of the ink can be adjusted with dispersants and extender pigments.

When each color filter sheet is formed by photolithography, a coloring composition prepared as a solvent developing or alkali developing type coloring resist is applied to a coloring composition by a coating method such as spray coating, spin coating, slit coating or roll coating. A dry thickness of 5 μm is applied to the transparent substrate. The film dried as needed is exposed to ultraviolet light through a mask having a predetermined pattern which is provided in contact with or not in contact with the film. Thereafter, the film is immersed in a solvent or an alkaline developer, or the developer is sprayed with a sprayer to remove the undeveloped portion to form a desired pattern, and the same procedure is repeated for other colors. In this way, a color filter can be prepared. In order to promote the polymerization of the coloring resist, heating is performed as needed. According to the photolithography method, it is possible to prepare a color filter which is more precise than a color filter prepared by a printing method.

In the development, an aqueous solution of sodium carbonate or sodium hydroxide can be used as the alkaline developer, and an organic base such as dimethylbenzylamine and triethanolamine can also be used. An antifoaming agent or a surfactant may be added to the developer.

In order to increase the sensitivity of ultraviolet exposure, ultraviolet exposure may be performed after coating and drying the colored resist, and coating of a water-soluble or alkali aqueous solution may dissolve a resin such as polyvinyl alcohol or a water-soluble acrylic resin and dry to form an oxygen-inhibited Polymerized film.

The color filter of the present invention 3 can also be produced by an electrolytic deposition method or a transfer method other than the above method. The coloring composition of the present invention can be used by any method. The electrolytic deposition method is a method in which individual color filter sheets are electrolytically deposited by means of electrophoresis of colloidal particles to form a transparent conductive film formed on a transparent substrate to form a color filter. Further, the transfer method is a method in which a color filter layer is previously formed on a separable transfer substrate, and then the color filter layer is transferred onto a desired transparent substrate.

(Example)

The invention will be described in detail hereinafter with reference to comparative examples of the examples and the conventional methods. However, the invention is not limited to these embodiments. In the embodiment, "parts" means "parts by weight" and "%" means "% by weight".

(Example 1)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride As a water-soluble inorganic salt, 100 parts of diglycolic acid as a water-soluble organic liquid and 5 parts of rosin resin (ester gum AT, supplied by Arakawa Chemical Industries, Ltd.) as a resin were almost uniformly premixed for 5 minutes. The obtained mixture was supplied to a continuous kneader 10 ("Miracle K.C.K.-type 42", supplied by Asada Iron Works. Co., LTD.) through a screw type metering feeder (metering feeder portion 4 in Fig. 1). The continuous kneading machine 10 has a feeding portion screw having a diameter of 120 mm φ and eight sets of kneading portions composed of a fixed disk and a rotating disk. The continuous kneader 10 was operated at a kneading temperature of 50 rpm and a kneading temperature of 90 ° C at a kneading composition extrusion amount of 21 kg / hr. The electric power consumption for kneading was 1.8 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained.

10 parts of the above pigment composition and 90 parts of varnish for gravure ink (nitrocellulose resin 12%, ethyl acetate 33%, toluene 30%, isopropanol 15% and methanol 10%) and 100 parts 3- Mm glass beads are mixed. The gravure ink was prepared by dispersing for 60 minutes with a paint regulator. The gravure ink was coated on the transparent film with a bar coater #4. White paper and black paper were placed on the back side of the thus obtained coated article. Colorimetry was performed separately using a colorimeter. The difference (ΔL*) of the luminance L* is 5.2. ΔL* is usually used as a standard for transparency. When ΔL* is large, the transparency is better.

Comparative Examples 1 and 2, which were kneaded by a conventional two-arm kneader having a capacity of 1000 parts by volume, are described below. Comparative Example 1 does not contain a resin which is a component of a normal kneading material. Although the electric power consumption amount in Example 1 was smaller than the electric power consumption amount in Comparative Example 1, the gravure ink coating material of Example 1 was superior in transparency to the gravure ink coating material of Comparative Example 1. Comparative Example 2 is the same as the use component of Example 1, and also includes a resin. The gravure ink-coated article of Comparative Example 2 was superior in transparency to the gravure ink-coated article of Comparative Example 1. The effect of adding a resin was thus found. However, the transparency in Example 1 was superior to Comparative Example 2. As the kneading device, the continuous kneading machine is superior to the two-arm kneading machine.

Comparative Examples 3 and 4 are explained below, in which the kneaded material contains no resin and the continuous kneader used in Example 1 is used. Although the kneading conditions of Comparative Example 3 were the same as those of Example 1, the gravure ink-coated article of Comparative Example 3 was inferior in transparency. Therefore, the effect of adding a resin in Example 1 can be recognized. Comparative Example 4 reduced the amount of the water-soluble organic liquid used in Comparative Example 3 and increased the kneading energy by doubling the electric power consumption. The transparency of the gravure ink-coated article in Comparative Example 4 was substantially the same as that of Comparative Example 3. When the kneaded material contains no resin, it is limited in improving the transparency of the gravure ink coated article.

Based on the above results, since a continuous kneader is used and a resin is mixed in the kneaded material, a pigment composition having a good actual quality represented by transparency can be obtained with a small amount of energy.

(Comparative Example 1)

100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, and 100 parts of diethylene glycol as a water-soluble organic liquid It was placed in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 90 ° C for 5 hours while the mixture was maintained in a dense slurry state. The electric power consumption required for kneading was 4.1 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained. A coated article was obtained in the same manner as in Example 1 using the above pigment composition. The ΔL* of the coated article was 1.2.

(Comparative Example 2)

100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, and 100 parts of diethylene glycol as a water-soluble organic liquid And 5 parts of rosin resin (ester gum AT, supplied by ATakawa Chemical Industries, Ltd.) was placed in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 90 ° C for 5 hours while the mixture was maintained in a dense slurry state. The electric power consumption required for kneading was 4.1 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained. A coated article was obtained in the same manner as in Example 1 using the above pigment composition. The ΔL ^* of the coated article was 2.3.

(Comparative Example 3)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHA ITOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride As a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid, it was almost uniformly premixed for 5 minutes. The mixture was kneaded and processed by a continuous kneader 10 in the same manner as in Example 1 to obtain a pigment composition. The electric power consumption required for kneading is 1.8 kwh per 1 kg of pigment. The coated product had a ΔL ^* of 3.6.

(Comparative Example 4)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYOI NKCO., LTD.) was used as an organic pigment, and 600 parts of sodium chloride was used as the organic solvent. The water-soluble inorganic salt and 80 parts of diethylene glycol were almost uniformly premixed as a water-soluble organic liquid for 5 minutes. The mixture was kneaded and processed by a continuous kneader 10 in the same manner as in Example 1 to obtain a pigment composition. The extrusion amount of the kneaded composition was 18 kg/hr. The electric power consumption required for kneading was 3.6 kwh per 1 kg of pigment. Its coated product had a ΔL ^* of 3.7.

(Examples 2 to 4)

In addition to the synthetic resin rosin (Dymerex resin, supplied by Rika Hercules), disproportionated rosin (Rondis R, supplied by Arakawa Chemical Industries, Ltd.) and hydrogenated rosin (Staybelite resin, supplied by Rika Hercules), respectively, in place of the resin, 1 A pigment composition was obtained in the same manner. Table 1 shows the amount of electric power consumption required for kneading and the ΔL ^* value of the coated article.

The ΔL ^{* of} each of the coated articles was larger than the values of Comparative Examples 1 to 4, and each of the coated articles had good transparency.

(Examples 5 to 7 and Comparative Examples 5 to 7)

The kneaded material having the components shown in Table 1 was kneaded separately under the kneading conditions shown in Table 1. These materials were separately treated in the same manner as in Example 1 to obtain a pigment composition. The organic pigment used in Example 5 and Comparative Example 5 was CI Pigment Yellow 138 (Paliotol Yellow K0691HD, supplied by BASF), and the organic pigment used in Example 6 and Comparative Example 6 was CI Pigment Red 177 (Chromophthal Red A2B, Provided by Ciba Specialty Chemicals Co.), the organic pigment used in Example 7 and Comparative Example 7 was CI, Sumiton Fast Violet RL Base (supplied by Sumitomo Chemical Co., Ltd.).

In Examples 5 to 7, the ΔL ^* value of the coated article prepared from the pigment composition obtained with a small amount of electric power consumption was larger than that in Comparative Examples 5 to 7, and the transparency in Examples 5 to 7 was very high. Ok.

Ex.=Example, CEx.=Comparative Example Ex.=Example, CEx.=Comparative Example

(Example 8)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride As the water-soluble inorganic salt, 100 parts of diethylene glycol as a water-soluble organic liquid, and 5 parts of the aforementioned compound (1) as a derivative, the mixture was almost uniformly premixed for 5 minutes. The obtained mixture was supplied to a continuous kneader 10 ("Miracle KCK-type 42", supplied by Asada Iron Works. Co., LTD.) through a screw type metering feeder (metering feeder portion 4 in Fig. 1). The continuous kneading machine 10 has a feeding portion screw having a diameter of 120 mm φ and eight sets of kneading portions composed of a fixed disk and a rotating disk. The continuous kneader 10 was operated at a kneading temperature of 50 kg at a kneading speed of 50 rpm and a kneading composition of 21 kg/hr. The electric power consumption required for kneading was 1.7 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained. According to the BET method, the pigment composition has a specific surface area of 90 m ² /g. 10 parts of the above pigment composition and 90 parts of varnish for gravure ink (nitrocellulose resin 12%, ethyl acetate 33%, toluene 30%, isopropanol 15% and methanol 10%) and 100 parts 3- Mm glass beads are mixed. The gravure ink was prepared by dispersing for 60 minutes with a paint regulator. The gravure ink was coated on the transparent film with a bar coater #4. The 60 of the thus obtained coated article was measured. - Gloss value. The gloss value was 82%.

Comparative Examples 8 and 9 are described below, in which kneading is carried out using a two-arm kneader having a usual capacity of 1000 parts by volume. Comparative Example 8 contained no derivative as a component of a conventional kneading material. Although the amount of electric power consumed in Example 8 was smaller than the amount of electric power consumed in Comparative Example 8, the specific surface area of the pigment composition of Example 8 was larger than that of Comparative Example 8 and the pigment composition of Example 8 was finely pulverized. The gravure ink coated article of Example 8 had a higher gloss value and thus had a good actual quality. Comparative Example 9 was the same as the component used in Example 8, and also included a derivative. The pigment composition of Comparative Example 9 had a larger specific surface area than Comparative Example 8, and the gravure ink coated article had a higher gloss value. Therefore, the effect of adding a derivative can be found. However, the effect in Example 8 was superior to that in Comparative Example 9. As the kneading device, the continuous kneading machine is superior to the two-arm kneading machine.

Comparative Examples 10 and 11 are explained below, in which the kneaded material contains no derivative and the continuous kneader used in Example 8 is used. Although the kneading conditions of Comparative Example 10 were the same as those of Example 8, the pigment composition of Comparative Example 10 had a small specific surface area and the gloss of the gravure ink-coated article was inferior. The effect of adding a derivative in Example 8 can be recognized. Comparative Example 11 lowered the amount of the water-soluble organic liquid used in Comparative Example 10 and increased the kneading energy by almost doubling the electric power consumption. In Comparative Example 11, the specific surface area of the pigment composition and the gloss value of the gravure ink-coated article were substantially the same as those in Comparative Example 10. When the composition of the kneaded material contains no derivative, it is limited in fineness and actual quality.

From the above results, it was found that since a continuous kneader was used and the derivative of the present invention was added to the kneaded material, fine powder of the pigment was used with a small amount of energy, and the actual quality was improved.

(Comparative Example 8)

100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, and 100 parts of diethylene glycol as a water-soluble organic liquid It was placed in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 100 ° C for 5 hours while the mixture was maintained in a dense slurry state. The electric power consumption required for kneading was 4.0 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained. According to the BET method, the pigment composition had a specific surface area of 69 m ² /g. A coated article was obtained in the same manner as in Example 8. The coated article had a gloss value of 66%.

(Comparative Example 9)

100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, and 100 parts of diethylene glycol as a water-soluble organic liquid And 5 parts of the aforementioned compound (1) were placed as a derivative in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 100 ° C for 5 hours while the mixture was maintained in a dense slurry state. The electric power consumption required for kneading was 4.1 kwh per 1 kg of pigment. The kneaded composition thus obtained was taken out and poured into 5,000 parts of water at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water and drying, whereby a pigment composition was obtained. According to the BET method, the pigment composition had a specific surface area of 77 m ² /g. A coated article was obtained in the same manner as in Example 8. The coated article had a gloss value of 72%.

(Comparative Example 10)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride As a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid, it was almost uniformly premixed for 5 minutes. This mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 8 to obtain a pigment composition. The electric power consumption required for kneading was 1.7 kwh per 1 kg of pigment. According to the BET method, the pigment composition has a specific surface area of 81 m ² /g. The coated article had a gloss value of 75%.

(Comparative Example 11)

Using a conversion mixer (supplied by Asada Iron Works. Co., LTD.), 100 parts of Blue 15 (T-95 crude blue, supplied by ZHUHAI TOYO INK CO., LTD.) as an organic pigment, 600 parts of sodium chloride As a water-soluble inorganic salt and 80 parts of diethylene glycol as a water-soluble organic liquid, the mixture was almost uniformly premixed for 5 minutes. This mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 8 to obtain a pigment composition. The kneaded composition was extruded at 18 kg/hr. The electric power consumption required for kneading was 3.5 kwh per 1 kg of pigment. According to the BET method, the pigment composition has a specific surface area of 82 m ² /g. The coated article had a gloss value of 76%.

(Examples 9 to 11)

A pigment composition was obtained in the same manner as in Example 8 except that the compound (2), the compound (3) and the compound (4) were used instead of the derivative used in Example 8. Table 2 shows the amount of electric power consumption required for kneading, the specific surface area according to the BET method, and the gloss value of the coated article.

The BET specific surface area of the pigment compositions in Examples 9 to 11 and the gloss value of the coated article were larger than those in Comparative Examples 8 to 11.

(Examples 12 to 14 and Comparative Examples 12 to 14)

The kneaded material having the components shown in Table 2 was kneaded separately under the kneading conditions shown in Table 2. These materials were separately treated in the same manner as in Example 8 to obtain a pigment composition. The organic pigments used in Example 12 and Comparative Example 12 were CI Pigment Red 122 (Hostaperm Pink E, supplied by Clariant), and the organic pigment used in Example 13 and Comparative Example 13 was CI Pigment Red 177 (Chromophthal Red A2B, Provided by Ciba Specialty Chemicals Co.), the organic pigment used in Example 14 and Comparative Example 14 was CI Pigment Violet 23 (Sumiton Fast Violet RL Base, supplied by Sumitomo Chemical Co., Ltd.).

The BET specific surface area of the pigment composition prepared in a small amount of electric power consumption in Examples 12 to 14 and the gloss value of the coated article were larger than those in Comparative Examples 12 to 14.

Ex.=Example, CEx.=Comparative Example Ex.=Example, CEx.=Comparative Example

The measurement method of the average primary particle diameter, the aspect ratio and specific surface area of the pigment, and the contrast of the resist coated film, and the preparation examples of the acrylic resin solution used in the examples will be explained before the subsequent examples.

The original particle size of the pigment was measured by a conventional method in which the size of the original particles was directly measured by an electron microscope. Specifically, the major axis diameter and the minor axis diameter of the pigment primary particles were measured, and the average value of the major axis diameter and the minor axis diameter was used as the particle diameter of the above pigment particles. For 100 or more pigment particles, the volume (weight) of each particle is individually obtained by taking an approximation of the hexahedron of the particle diameter obtained as above, and the volume average particle diameter is used as the average primary particle diameter. In the measurement by transmission electron microscopy (TEM) and scanning electron microscopy (SEM), almost the same results were obtained.

The aspect ratio of the pigment was obtained by separately measuring the major axis diameter and the minor axis diameter of the pigment primary particles with an electron microscope and calculating according to the following equation. The aspect ratio, preferably the approximate square shape of the particles, has an aspect ratio of approximately 1.

(Aspect ratio) = (long axis diameter) / (short axis diameter)

The specific surface area of the pigment particles was obtained by the BET method based on nitrogen adsorption. The measurement was performed using an automatic vapor adsorption amount measuring instrument ("BELSORP 18", supplied by BEL Japan Inc.).

Then, a method of measuring the contrast of the coating film prepared using the resist will be described with reference to FIG. Light emitted from the backlight element (7) for the liquid crystal display passes through the polarized polarizing plate (6), and the polarized light passes through the dried coating film (4) of the colored composition coated on the glass substrate (5) and reaches Polarizer (3). When the plane of polarization of the polarizing plate (6) is parallel to the plane of polarization of the polarizing plate (3), the polarizing plate (3) transmits light. When the plane of polarization is vertical, the polarizing plate (3) blocks light. However, when the light polarized by the polarizing plate (6) passes through the dry coating film (4) of the coloring composition, scattering occurs due to the pigment particles and an offset occurs on the partially polarized surface. In this case, when the polarizing plates are parallel, the amount of light transmitted through the polarizing plate (3) is lowered. When the polarizing plate is vertical, the polarizing plate (3) transmits a part of the light. The transmitted light is measured as the brightness on the polarizing plate. The ratio (contrast) of the brightness when the polarizing plates are parallel and the brightness when the polarizing plates are vertical is calculated.

(contrast) = (parallel brightness) / (vertical brightness)

Therefore, when scattering occurs due to the coloring composition drying the pigment in the coating film (4), the parallel brightness is lowered and the vertical brightness is increased. Therefore, the contrast is lowered.

A color luminance meter ("BM-5A", supplied by Topcon) was used as a luminance meter (1), and a polarizing plate ("NPF-G1220DUN", supplied by Nitto Denko Corporation) was used as a polarizing plate. In the measurement, a black mask (2) having a square hole of 1 × 1 cm was placed on the measuring portion to block unnecessary light.

(Preparation Example of Acrylic Resin Solution Used in the Example)

800 parts of cyclohexanone was placed in the reactor, which was heated to 100 ° C together with nitrogen gas introduced into the reactor. A mixture of 60.0 parts of styrene, 60.0 parts of methacrylic acid, 65.0 parts of methyl methacrylate, 65.0 parts of methyl butyl acrylate and 10.0 parts of azobisisobutyronitrile was added dropwise to the reactor at the same temperature for more than 1 hour. To carry out the polymerization. After the dropwise addition, the resulting mixture was further reacted at 100 ° C for 3 hours. Then, a solution of 2.0 parts of azobisisobutyronitrile in 50 parts of cyclohexanone was added. The mixture was further reacted for 1 hour to obtain an acrylic resin solution having a weight average molecular weight of about 40,000 as measured by GPC.

The acrylic resin solution was cooled to room temperature, and then a part of the resin solution was sampled. The sample resin solution was dried at 180 ° C for 20 minutes and the content of nonvolatiles was measured. The cyclohexanone was added to the resin solution so that the content of the nonvolatile matter became 20%, thereby preparing an acrylic resin solution.

(Example 15)

Nearly uniformly premix 100 parts of crude copper indigo ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 100 parts with a conversion mixer (supplied by Asada Iron Works. Co., LTD.) Sodium chloride and 10 parts of diethylene glycol were added for 5 minutes. The obtained mixture was supplied to a continuous kneader ("Miracle KCK-type 42", by Asada Iron Works. Co., LTD.) and kneaded by a screw type metering feeder (metering portion 4 in Fig. 1). . The continuous kneader has a feeding portion screw diameter of 120 mm φ and eight sets of kneading portions composed of a fixed disk and a rotating disk. The continuous kneader was operated at a crushing temperature of 50 rpm and a pulverizing temperature of 100 ° C at a kneading composition extrusion amount of 21 kg / hr. The kneaded material thus obtained was taken out and poured into 1,300 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine copper indigo pigment was obtained. The fine copper phthalocyanine pigment has a specific surface area of 111 m ² /g. When observed by TEM (electron microscopy), the average primary particle diameter was 23.1 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.61.

Then, a mixture having the following components containing the fine copper indigo pigment obtained above was uniformly stirred, and then dispersed using an Eiger mill ("Minimodel M-250 MKII", supplied by Eiger Japan) using a zirconia bead having a diameter of 1 mm for 5 hours. Filtered with a 5 μm screening procedure to prepare a blue pigment dispersion.

Fine copper indigo pigment 10.0 parts Derivative 48 (pigment derivative) 1.0 part phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

Further, a mixture having the following components containing the blue colored dispersion obtained above was uniformly stirred and mixed, and then filtered using a 1 μm screening procedure to prepare an alkali-developing blue resist.

Blue coloring dispersion 45.0 parts of acrylic resin solution 15.0 parts of trimethylolpropane triacrylate 9.0 parts ("NK ester ATMPT", supplied by Shin-Nakamura Chemical Co., Ltd.) Photopolymerization initiator 2.0 parts (" Irgacure 907", supplied by Ciba Specialty Chemicals Co.) sensitizer 0.2 parts ("EAB-F", supplied by Hodogaya Chemical Co., Ltd.) 28.8 parts of cyclohexanone

(Comparative Example 15)

100 parts of crude copper indigo ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 100 parts of sodium chloride and 10 parts of diethylene glycol were placed in a volume of 1000 parts by volume. Kneading machine. The mixture was kneaded at 100-110 ° C for 5 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 1,300 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine copper indigo pigment was obtained. The fine copper phthalocyanine pigment has a specific surface area of 93 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle diameter was 72.3 nm and the aspect ratio was 1.75.

An alkali-developing blue resist was prepared in the same manner as in Example 15 using the fine copper indigo pigment obtained above.

(Embodiment 16)

Supply and implementation of a kneaded composition containing 100 parts of quinophthalone pigment (CI Pigment Yellow 138, "Paliotol Yellow K0961HD", supplied by BASF), 3,000 parts of sodium chloride, and 700 parts of ethylene glycol In the same kneading machine used in Example 15, the composition was kneaded at a kneading composition of 25 kg/hr at a spindle rotation speed of 50 rpm and a grinding temperature of 110 °C. The kneaded material thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine quinolone pigment. The fine quinolone pigment has a specific surface area of 115 m ² /g. When observed by TEM (electron microscopy), the average primary particle diameter was 33.2 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.53.

Then, a mixture having the following components containing the fine quinolone pigment obtained above was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a yellow pigment dispersion. Further, an alkali-developing yellow resist was prepared in the same manner as in Example 15 using the yellow pigment dispersion obtained above.

Fine quinolone pigment 10.0 parts derivative 39 (pigment derivative) 1.0 part phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

(Comparative Example 16)

100 parts of quinolone pigment (CI Pigment Yellow 138, "Paliotol Yellow K0961HD", supplied by BASF), 3,000 parts of sodium chloride and 700 parts of ethylene glycol were placed in a 1000-volume double-arm kneader in. The mixture was kneaded at 100-110 ° C for 6 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 1,300 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine quinolone pigment was obtained. The fine quinolone pigment has a specific surface area of 95 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle diameter was 82.5 nm and the aspect ratio was 1.72.

An alkali-developing yellow resist was prepared in the same manner as in Example 16 using the fine quinolone pigment obtained above.

(Example 17)

A kneaded composition containing 100 parts of a diketopyrrolopyrrole pigment (CI Pigment Red 254, "IRGAPHOR RED B-CF", supplied by Ciba Specialty Chemicals Co.), 2,000 parts of sodium chloride, and 230 parts of ethylene glycol. The mixture was supplied to the same kneader as used in Example 15, and the composition was kneaded at a kneading composition of 23 kg/hr at a spindle rotation speed of 50 rpm and a grinding temperature of 60 °C. The kneaded material thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine diketopyrrolopyrrole pigment. The fine diketopyrrolopyrrole pigment has a specific surface area of 122 m ² /g. When observed by TEM (electron microscopy), the average primary particle diameter was 35.2 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.61.

Then, a mixture having the following components containing the fine diketopyrrolopyrrole pigment obtained above was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a red pigment dispersion. Further, an alkali-developing red resist was prepared in the same manner as in Example 15 using the red pigment dispersion obtained above.

Fine diketopyrrolopyrrole pigment 10.0 parts of derivative 49 (pigment derivative) 1.0 part of phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

(Comparative Example 17)

100 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254, "IRGAPHOR REDB-CF", supplied by Ciba Specialty Chemicals Co.), 2,000 parts of sodium chloride and 230 parts of ethylene glycol were placed in a volume of 1000 volumes. The two arms are kneaded in the machine. The mixture was kneaded at 65-75 ° C for 6 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 20,000 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine diketopyrrolopyrrole pigment was obtained. The fine diketopyrrolopyrrole pigment has a specific surface area of 105 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle size was 69.5 nm and the long and wide pyrogram was 1.81.

An alkali-developing red resist was prepared in the same manner as in Example 17 using the fine diketopyrrolopyrrole pigment obtained above.

(Embodiment 18)

Will contain 100 parts of crude two A purple pigment (Sumiton Fast Violet RL Base, supplied by Sumitomo Chemical Co., Ltd.), a kneaded composition of 1,000 parts of sodium chloride and 150 parts of ethylene glycol was supplied to the same kneading machine as used in Example 15. The composition was kneaded at a kneading composition of 22 kg/hr at a spindle rotation speed of 50 rpm and a grinding temperature of 100 °C. The kneaded material thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine two. Purple pigment. The fine two The purple pigment has a specific surface area of 140 m ² /g.

It was observed by TEM (electron microscopy) that the average primary particle diameter was 30.3 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.63.

Then, the uniform agitation has a fine second obtained from the above A mixture of the following components of the purple pigment was then dispersed and filtered in the same manner as in Example 15 to obtain a purple pigment dispersion. Further, an alkali-developing-type purple resist was prepared in the same manner as in Example 15 using the purple pigment dispersion obtained above.

Fine two Purple pigment 10.0 parts Derivative 48 (pigment derivative) 1.0 part phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

(Comparative Example 18)

100 parts of crude two A purple pigment (Sumiton Fast Violet RL Base, supplied by Sumitomo Chemical Co., Ltd.), 1,000 parts of sodium chloride, and 150 parts of diethylene glycol were placed in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 100-110 ° C for 5 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 10,000 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, thereby obtaining a fine two. Purple pigment. Fine two The purple pigment has a specific surface area of 93 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle diameter was 59.5 nm and the aspect ratio was 1.85.

The fine two obtained above was used in the same manner as in Example 18. A purple pigment is used to prepare an alkali-developing purple resist.

(Embodiment 19)

It will contain 100 parts of crude copper indigo pigment ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of rosin resin as resin. The kneaded composition was supplied to the same kneader as used in Example 15, and the composition was kneaded at a kneading speed of 90 kg at a spindle rotation speed of 50 rpm and a grinding temperature of 90 °C. The kneaded material thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine copper indigo pigment. The fine crude copper indigo pigment has a specific surface area of 128 m ² /g. When observed by TEM (electron microscopy), the average primary particle diameter was 21.1 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.54.

Then, a mixture having the following components containing the fine crude copper indigo pigment obtained above was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a blue pigment dispersion. Further, an alkali-developing blue resist was prepared in the same manner as in Example 15 using the blue pigment dispersion obtained above.

Fine copper indigo pigment 10.0 parts Derivative 48 (pigment derivative) 1.0 part phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

(Comparative Example 19)

100 parts of crude copper indigo pigment ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of rosin resin as a resin It is 1000 parts by volume of the two-arm kneading machine. The mixture was kneaded at 90 ° C for 5 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 1,300 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine crude copper indigo pigment was obtained. The fine crude copper indigo pigment has a specific surface area of 97 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle diameter was 68.9 nm and the aspect ratio was 1.71.

An alkali-developing blue resist was prepared in the same manner as in Example 15 using the fine crude copper indigo pigment obtained above.

(Embodiment 20)

It will contain 100 parts of crude copper indigo pigment ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of derivative 51 (pigment derived) The kneaded composition of the product was supplied to the same kneader as used in Example 15, and the composition was kneaded at a kneading composition of 22 kg/hr at a spindle rotation speed of 50 rpm and a grinding temperature of 100 °C. Things. The kneaded material thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine copper indigo pigment. The fine crude copper indigo pigment has a specific surface area of 132 m ² /g. When observed by TEM (electron microscopy), the average primary particle diameter was 20.2 nm, and all the pigment particles were finely pulverized and no coarse particles were found. The aspect ratio is 1.50.

Then, a mixture having the following components containing the fine crude copper indigo pigment obtained above was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a blue pigment dispersion. Further, an alkali-developing blue resist was prepared in the same manner as in Example 15 using the blue pigment dispersion obtained above.

Fine copper indigo pigment 10.0 parts Derivative 48 (pigment derivative) 1.0 part phosphate ester pigment dispersant ("BYK111", supplied by BYK Chemie) 1.0 part acrylic resin solution 40.0 parts cyclohexanone 48.0 parts

(Comparative Example 20)

100 parts of crude copper indigo pigment ("T-95 crude blue", supplied by ZHUHAI TOYO INK CO., LTD.), 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of derivative 51 (pigment derivative) ) placed in a two-arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 100 ° C for 5 hours while the mixture was maintained in a dense slurry state. After grinding, the resulting mixture was taken out and poured into 1,300 parts of a 1% sulfuric acid solution at 70 °C. The mixture was stirred at a temperature for 1 hour, followed by filtration, washing with water, drying and pulverization, whereby a fine crude copper indigo pigment was obtained. The fine blister copper indigo pigment has a specific surface area of 99 m ² /g. It was observed by TEM (electron microscopy) that the pigment particles were all finely pulverized and no coarse particles were found. However, the average primary particle diameter was 66.3 nm and the aspect ratio was 1.69.

An alkali-developing blue resist was prepared in the same manner as in Example 15 using the fine crude copper indigo pigment obtained above.

Table 3 shows the measurement results of the specific surface area, the average primary particle diameter, and the aspect ratio of the fine pigments obtained in Examples 15 to 20 and Comparative Examples 15 to 20.

For each of the resists obtained in Examples 15 to 20 and Comparative Examples 15 to 20, three coated substrates having different film thicknesses were prepared. Each film thickness and each contrast was measured. The contrast at a film thickness of 2 μm was obtained from the data of the above three coated substrates by the original correlation method. The resist was applied to the substrate by changing the number of revolutions of the spin coater used so that each of the prepared coated substrates had a dry film thickness of about 1 μm, and then dried in a hot air tank at 80 ° C for 30 minutes. .

The contrast ratio of the coated substrate prepared by using the resists obtained in Examples 15 to 20 was higher than that of the coated substrates prepared using the resists obtained in Comparative Examples 15 to 20.

Ex.=Example CEx.=Comparative example

1. . . Feeding section

2. . . Kneading part

3. . . Discharge part

4. . . Metering feeder section

10. . . Continuous kneading machine

11. . . shell

12. . . Auger

twenty one. . . Fixed disk

21a. . . Cavity fan-shaped fixed disk

21c. . . Cavity rose fixed plate

21e. . . Cavity dome

twenty two. . . Kneading cylinder

twenty three. . . Rotating disk

23b. . . Cavity fan rotating disk

23d. . . Cavity rose-shaped rotating disk

23f. . . Cavity-shaped rotating disk

twenty four. . . Screw

41. . . Raw material funnel

42. . . Screw feeder

43. . . Connecting cylinder

44. . . Intermediate cylinder

111. . . Raw material inlet

121. . . transmission shaft

122. . . Spiral fin

211. . . Active mounting hole

212. . . Cavity

231. . . Assembly hole

232. . . Cavity

(1). . . Luminance meter

(2). . . Black mask

(3). . . Polarizer

(4). . . Dry coating film

(5). . . Glass matrix

(6). . . Polarizer

(7). . . Backlight component

Fig. 1 is a cross-sectional side view showing a specific example of a continuous kneading machine used in the present invention.

Fig. 2 is a front view and a rear view showing a fixed disk and a rotary disk employed in a specific example of the continuous kneading machine shown in Fig. 1. In Fig. 2, (a) is a cavity-sector-shaped fixed disk, (b) is a cavity sector-shaped rotating disk, and (c) is a cavity-rose-shaped fixed disk. (d) is a cavity rose-shaped rotating disk, (e) is a cavity-mortar-shaped fixed disk, and (f) is a cavity-shaped rotating disk.

Figure 3 is a schematic diagram of a measuring device for measuring contrast.

1. . . Feeding section

2. . . Kneading part

3. . . Discharge part

4. . . Metering feeder section

10. . . Continuous kneading machine

11. . . shell

12. . . Auger

twenty one. . . Fixed disk

twenty two. . . Kneading cylinder

twenty three. . . Rotating disk

twenty four. . . Screw

41. . . Raw material funnel

42. . . Screw feeder

43. . . Connecting cylinder

44. . . Intermediate cylinder

111. . . Raw material inlet

121. . . transmission shaft

122. . . Spiral fin

Claims (10)

A method for preparing a pigment composition comprising kneading a mixture comprising an organic pigment, a water-soluble inorganic salt, a water-soluble organic liquid and a resin by a continuous kneader comprising a drive shaft, a ring-shaped fixing plate, and a concentric disk And the entire rotating disk that rotates around the axis of the drive shaft and the pulverizing space formed in the gap between the fixed disk and the rotating disk. The method of claim 1, wherein the resin is a rosin resin. A method for producing a pigment composition comprising kneading a mixture comprising: an organic dye derivative represented by the formula (1) and a compound represented by the formula (3) by a continuous kneader Any one of the derivatives, each of which contains at least one substituent selected from the group consisting of a quinone iminomethyl group, an amine group, a sulfonic acid group or a carboxylic acid group; P-{X ₁ -(Y ₁ )k }m (1) wherein P represents an organic dye residue; X ₁ is a single bond or represents -SO ₂ - or -CO-; Y ₁ is a fluorenylene methyl group which may be substituted by a nitro group or a halogen atom, - NR ₂ R ₃ , -SO ₃ . M/n or -COO. M/n; wherein R ₂ and R ₃ each independently represent an alkyl group, M represents a hydrogen ion, a metal ion having a valence of 1 to 3 or an ammonium ion substituted with at least one alkyl group, n is a valence of M; k is 1 Or an integer of 2; and m is an integer from 1 to 4, Where R represents three Residue; X ₃ -X _{5 are} each independently a single bond or represent -O-, -S-, -CO-, -SO ₂ -, NR ₁ -, -CONR ₁ -, -SO ₂ NR ₁ -, - NR ₁ CO- or -NR ₁ SO ₂ -, a linear or branched alkylene group having 1 to 12 carbon atoms, a benzene residue which may be substituted by an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group or a halogen atom a group or a combination linking group containing at least two linking groups, wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; and Y ₃ is a quinone imidomethyl group which may be substituted by a nitro group or a halogen atom, -NR ₂ R ₃ , -SO ₃ . M/n or -COO. M/n; wherein R ₂ and R ₃ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted phenyl group, or R ₂ Together with R ₃ form a substituted or unsubstituted heterocyclic ring which may contain an additional nitrogen atom, an oxygen atom or a sulfur atom, M represents a hydrogen ion, a metal ion having a valence of 1 to 3 or at least one alkyl group a substituted ammonium ion, n is a valence of M; Y ₄ and Y ₅ each independently have the same definition as Y ₃ or represent an alkyl group, an amine group, a nitro group, a hydroxyl group, an alkoxy group, a halogen atom, or a a substituted or unsubstituted phenyl group; and p, q and r are each independently an integer of 1 or 2; an organic pigment; a water-soluble inorganic salt; and a water-soluble organic liquid; the continuous kneader comprising a drive shaft and a ring-shaped fixing plate a rotating disk concentric with the fixed disk and rotating around the axis of the drive shaft and a pulverizing space formed in a gap between the fixed disk and the rotating disk. For example, the method of claim 1 is that the organic pigment is an azo pigment, an indigo pigment, a quinophthalone pigment, an isoindolinone pigment, an isoporphyrin pigment, a perylene pigment, an anthrone pigment. , diketopyrrolopyrrole pigment, sulphur blue pigment, two Pigments, quinolone pigments, anthraquinone pigments or anthraquinone pigments. A coloring composition for a color filter comprising a pigment carrier and a pigment having a transparent resin, a precursor thereof or a mixture thereof, wherein the pigment comprises kneading an organic pigment, a water-soluble inorganic salt and a water-soluble substance by a continuous kneader a fine organic pigment obtained by a mixture of organic liquids comprising a drive shaft, an annular fixed disk, a rotating disk concentric with the fixed disk and rotating around the axis of the drive shaft, and a gap between the fixed disk and the rotating disk The smashing space formed. The coloring composition of claim 5, wherein, in the mixture, 1 to 30 parts by weight of the water-soluble inorganic salt and 0.1 to 7 parts by weight of the water-soluble organic liquid are contained per 1 part by weight of the organic pigment. The colored composition of claim 5, wherein the mixture containing the organic pigment, the water-soluble inorganic salt and the water-soluble organic liquid is kneaded at a kneading temperature of 10 to 150 °C. The colored composition of claim 5, wherein the mixture containing the organic pigment, the water-soluble inorganic salt and the water-soluble organic liquid further comprises a resin. The colored composition of claim 5, wherein the mixture containing the organic pigment, the water-soluble inorganic salt and the water-soluble organic liquid further comprises a pigment derivative. A color filter comprising a color filter segment formed by the colored composition of claim 5 of the patent application.